o-Nitrophenylpropiolic acid

Base Information

• Chemical Name: o-Nitrophenylpropiolic acid
• CAS No.: 530-85-8
• Deprecated CAS: 92458-21-4
• Molecular Formula: C9H5 N O4
• Molecular Weight: 191.143
• Hs Code.: 2916399090
• European Community (EC) Number: 208-496-2
• NSC Number: 20556
• UNII: R95562375X
• DSSTox Substance ID: DTXSID00870588
• Nikkaji Number: J7.402K
• Wikidata: Q27287988
• Mol file: 530-85-8.mol

Synonyms:530-85-8;o-Nitrophenylpropiolic acid;3-(2-Nitrophenyl)propiolic acid;2-Nitrophenylpropiolic acid;3-(2-nitrophenyl)prop-2-ynoic acid;2-Propynoic acid, 3-(2-nitrophenyl)-;3-(2-Nitrophenyl)-2-propynoic acid;Propiolic acid, (o-nitrophenyl)-;UNII-R95562375X;EINECS 208-496-2;NSC 20556;NSC-20556;R95562375X;3-{2-nitrophenyl}-2-propynoic acid;2-NITROPHENYLPROPIOLICACID;o-Nitrophenylpropiolsaure;2-Nitrophenylpropalic acid;Oprea1_581205;SCHEMBL1652756;3-(2-Nitrophenyl)propiolicacid;DTXSID00870588;o-NitrophenylpropiolsA currencyure;NSC20556;STK260095;AKOS005424319;O-NITROPHENYLPROPIOLIC ACID [MI];FT-0694556;A914482;AG-777/36178015;Q27287988

Chemical Property of o-Nitrophenylpropiolic acid

Chemical Property:

• Vapor Pressure: 3.03E-07mmHg at 25°C
• Melting Point: ~157° with decompn
• Refractive Index: 1.635
• Boiling Point: 403.8°Cat760mmHg
• PKA: 1.52±0.10(Predicted)
• Flash Point: 182.5°C
• PSA: 83.12000
• Density: 1.47g/cm³
• LogP: 1.55410
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 191.02185764
• Heavy Atom Count: 14
• Complexity: 306

Purity/Quality:

98%min ^*data from raw suppliers

3-(2-Nitrophenyl)propiolicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C#CC(=O)O)[N+](=O)[O-]
• Uses: As a reagent for alkaloids and glucose.

Technology Process of o-Nitrophenylpropiolic acid

There total 15 articles about o-Nitrophenylpropiolic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

carbon dioxide (124-38-9,18923-20-1) + trimethyl((2-nitrophenyl)ethynyl)silane (75867-47-9) → 3-(2-nitrophenyl)-2-propynoic acid (530-85-8)

Guidance literature:

With cesium fluoride; In dimethyl sulfoxide; at 20 ℃; for 3h;

DOI:10.1002/adsc.201700122

Reference yield: 78.0%

methyl (2-nitrophenyl)propiolate (7515-14-2) → 3-(2-nitrophenyl)-2-propynoic acid (530-85-8)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jm900553j

Reference yield:

2,3-dibromo-3-(2-nitro-phenyl)-propionic acid ethyl ester (35283-00-2) → ethanol (64-17-5) + 3-(2-nitrophenyl)-2-propynoic acid (530-85-8) + hydrogen bromide (10035-10-6,12258-64-9)

Guidance literature:

upstream raw materials:

(E)-ethyl 3-(2-nitrophenyl)acrylate

2,3-dibromo-3-(2-nitrophenyl)propanoic acid

phenylpropyolic acid

2,3-dibromo-3-(2-nitro-phenyl)-propionic acid ethyl ester

Downstream raw materials:

1H,1H'-2,2'-Biindolylidene-3,3'-dione

4-oxo-1,4-dihydrocinnoline-3-carboxylic acid

Indican

ortho-nitrobenzoic acid

Refernces

• 1、 Marien, Niels,Luo, Ting,Verniest, Guido. "Synthesis of Piperidinone and Azepanone Fused Indoles via a Wagner-Meerwein Type 1,2-Amide Migration of 2-Spiropseudoindoxyls". supporting information. p. 934 - 938. Retrieved 2017/05/05.
• 2、 Marien, Niels,Brigou, Ben,Pinter, Balazs,De Proft, Frank,Verniest, Guido. "Synthesis of 2-spiropseudoindoxyls via an intramolecular nitroalkyne redox-dipolar cycloaddition cascade". supporting information. p. 270 - 273. Retrieved 2015/03/05.